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The synthesis and characterization of novel ionic liquid crystals based on pyridinium salts with Br⁻ and PF₆⁻ counterions are described in this work. These pyridinium salts were derived from 4-hydroxypyridine, both by <i>N</i>- and <i>O</i>-alkylation. The 3,4,5-tri(alkyloxy)-benzyl mesogenic unit was attached to the nitrogen atom of the pyridinium ring. Alkyl chains with a different number of carbon atoms (6, 8, 10, 12 and 14) were employed in order to show the effect on the stability of mesophase. The POM (polarizing optical microscopy) and XRD (powder X-ray diffraction) studies indicated that bromide salts with shorter chains C₆, C₈ and C₁₀ do not show mesomorphic properties, while longer chain analogues with C₁₂ and C₁₄ exhibit two enantiotropic columnar phases. Surprisingly, the pyridinium salts with the larger size PF₆⁻ counterion do not exhibit liquid crystal properties.